1025966-70-4

Upstream product

• 75-44-5 phosgene 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 503-38-8 trichloromethyl chloroformate 
• 100-52-7 benzaldehyde 

Downstream Products

• 68975-07-5 3-benzyltetrahydrofuran-2-one 
• 372076-42-1 (E)-4-phenyl-3-butenyl azidoformate 
• 142636-17-7 O-((E)-4-phenylbut-3-en-1-yl) Se-phenyl selenocarbonate 

Relevant academic research and scientific papers

Synthesis and mechanistic study of fused 2-pyrrolines via thermolysis of 6-substituted-3,5-hexadienyl azidoformates

Thermolysis of 3,5-hexadienyl azidoformates at 300 °C, 0.05 Torr, led to a fused 2-pyrroline regiospecifically, regardless of the configuration E or Z between the C-3 and C-4 double bond. Thermolysis of 6-substituted-3,5(E)-hexadienyl azidoformates yielded a kinetically controlled 2-pyrroline with cis configuration between H-1 and H-8a whereas 6-substituted-3,5(Z)-hexadienyl azidoformates produced a cis and trans mixture. The mechanism was proposed as the loss of nitrogen to form an acyl nitrene, then addition to a double bond to produce an aziridine. Finally the cleavage of the C-C bond generated a vinylazomethine ylide followed by recyclization to a fused 2-pyrroline.

Synthesis of γ- and δ-Lactones by Free-Radical Annelation of Se-Phenyl Selenocarbonates

A general method for the synthesis of γ- and δ-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described.This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction.Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield.Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.